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Murray Zemelman - lingerie mogul, a.k.a. the Bra King - wakes up one morning, starts his car in the confines of his airtight garage, and contemplates the worst. But instead of doing himself in, he pops a Prozac and hits the road, waving good-bye to his trophy wife, the thriving brassiere business, and the streets of New Jersey for good. He's headed to Florida, home of his first wife, Franny, whom he was stupid enough to leave all those years ago. But now he wants to start fresh. Is it a brilliant insight? A glitch in his Prozac dosage? Who cares? He's off to Key West.
There, he meets Tommy Tarpon, a local Native American - beaten down and made bitter by the unfairness of life around him, and the last surviving member of his small Florida tribe. Together they cook up a plan: with Murray's business acumen and Tommy's ability to make the most of government statutes, Key West could very well get its first legal gambling parlor on Tommy's tribal grounds - a tiny, alligator-infested island just off the coast.
But gambling in Key West isn't an original idea, and a whole other species of reptiles is interested in the plan. With the "assistance" of Key West's crookedest politician, a local Mafioso makes Murray and Tommy an offer they can't refuse. All Murray wanted was to woo his first wife away from her reading group and into the Jacuzzi - but he ends up getting her, himself, and Tommy into more hot water than he ever bargained for.

A pill-popping lingerie businessman, Murray Zemelman leaves his "boring" life in New Jersey to go to Key West, where he and his Native American friend find themselves fighting to save their money, lives, and new business (Key West's first legal gambling parlor) from a local mafioso. Tour.